


Pretty (Sexy)

by Marveljunkie



Series: Write Me [9]
Category: Supernatural
Genre: Feminization, Hand Jobs, Kissing, M/M, Men of Letters Bunker, Pampering, Sam In Panties, Sam in Makeup, Season 11, ish
Language: English
Status: Completed
Published: 2017-04-09
Updated: 2017-04-09
Packaged: 2018-10-17 02:31:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 667
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10584576
Author URL: https://archiveofourown.org/users/Marveljunkie/pseuds/Marveljunkie
Summary: Sometimes, Sam likes to feel pretty.





	

**Author's Note:**

> I have no idea where this came from. I'm not that big into feminization and shit but as I was trying to come up with a thing today, my fancy pear scented lotion caught my eye and wouldn't leave me alone!
> 
> Thanks again to Katie for helping me decide between Sam and Dean! (I couldn't make up my mind who I should dress up.)
> 
> Also, I prefer to think of Sam in this fic as more gender fluid(ish). He's not really trans, he just finds it nice and relaxing to dress like a girl (and Dean finds it sexy so win win ;))

Sometimes, Sam likes to feel pretty. 

Today is one of those days. He waits rather impatiently til Dean leaves to run errands and then shuts himself in the bathroom with his deep emerald-green satin bag of toiletries. 

Sam unpacks it, laying out the items in their proper places. Shaving cream and razor, scented body scrub, and bubbles for the bath go by the tub. 

The hair serum, blow dryer, facial cleanser, and makeup go on the sink. 

And on the towel rack, Sam hangs his decidedly more feminine clothing, a pair of pink and white lace panties and a light blue nightgown. (He was never much for bras.) 

Then he gets to work. 

First, the bath. Sam soaks in pleasantly hot water, taking his time with the wash. After getting out and drying off, he rubs lotion onto the freshly shaved skin and gently towels his hair.

Then, after rubbing in a palm full of serum, he blow dries his hair into soft waves. He wraps the towel around his waist and does his makeup carefully. A little bit of eyeliner and eye-shadow, and special mascara to emphasize his eyelashes, and some lipstick. 

He inspects himself in the mirror and nods. Already he looks decidedly more feminine and he feels softer, prettier. 

The panties and lacy nightgown complete the look. And if he wasn't 6'4" and nearly two hundred pounds, Sam swears he could be a girl. 

Suddenly he remembers one last thing. He fishes into the green bag, reaching into the inner pocket for his garter belt and stockings. 

This part isn't so much for his as it is for Dean. Sam grins as he rolls the stockings up his smooth legs and hooks them to the belt. Dean will love this.

He puts the things back into the bag and heads to his room. Dean still isn't home, so he stretches out gingerly on his back in bed. Might as well nap a little til Dean gets home. 

******

"Sammy?" Dean calls, stepping inside. "I got you rabbit food!"

No answer. Dean shrugs. He must be asleep. He heads down the hall to Sam's room and pushes the door open. 

What he sees makes him stop short. Fuck. So it's one of these days, eh? He can so get behind that. He gives his dick a firm rub as it hardens and steps inside. 

Slowly, Dean tiptoes into the room and sits down on the bed next to Sam. God, he's so gorgeous. He strokes a finger over Sam's cheek and tickles his long long eyelashes with a his fingertip.

Sam's eyelashes flutter open and Dean grins. "Hey, pretty girl." He croons. "Waiting for me?"

Sam blushes shyly, like he always does, and Dean grins wider. He slides his hand down his brothers flat chest, tweaking a nipple through the fabric. 

Sam bites his lip and Dean leans down to kiss him softly. "You're so pretty, baby." He whispers. "Goddamn beautiful." The compliment makes Sam whimper quietly and Dean slides his hand down to cup his lace covered dick. Fuck, Sam shaved. Dean groans. 

"So hard for me already." Dean murmurs. "So good." He grasps Sam's dick firmly, stroking the hardening member. He pulls back just enough to watch Sam gasp and moan.

Sam pries his eyes open and stares up at Dean as he gets close. Fuck, but these are the moments he really loves. When he's almost there and Dean strokes him faster, looking at him like--

Sam's vision whites out and he arches up with a moan as he comes, staining the panties. 

Dean moans and kisses him again. Sam pants against his brothers lips, gasping through the aftershocks. Distantly, he registers Dean coming. 

After a while they separate, and Sam grins dopily up at Dean. He can't wait til Dean turns him over and fucks him with the panties pushed aside. 

He loves feeling pretty. The sexy Dean makes him feel is just a wonderful thick layer of icing on the cake.

**Author's Note:**

> I'm sorry if it seems a little scrambled, I have a headache. If something is glaringly obvious and bothers you, feel free to leave a polite comment and I'll try and fix the problem. 
> 
> Thanks for reading!


End file.
